Synthesis and polymerization of vinylcyclopropanes

Moszner, Norbert; Zeuner, Frank; Völkel, Thomas; Rheinberger, Volker

doi:10.1002/(sici)1521-3935(19991001)200:10<2173::aid-macp2173>3.3.co;2-1

Cited by 31 publications

(62 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The monomer 1a is a white crystalline substance, whereas 1b is a colorless, highly viscous liquid that is advantageous for practical application. The monomers are stable in the presence of moisture or inorganic dental fillers in contrast to previously investigated 2‐methylene‐1,3‐dioxepanes 10. In the case of monomer 1b, the investigation of the crude product by LC‐MS showed (see Fig.…”

Section: Resultsmentioning

confidence: 75%

“…Furthermore, the 1‐(1‐ethoxycarbonyl‐2‐vinylcyclopropane‐1‐oyl)urea (D) and the 1‐ethoxycarbonyl‐2‐vinylcyclopropane‐1‐carboxylic anhydride (F) are also formed in a quantity of less than about 1.0 wt %. In the meantime, the new compounds (A), (C), and (F) were synthesized 11…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, monomers 1a and 1b are used to substitute TEGDMA in dental composites, which results in both a decrease in the linear shrinkage and a change of the shrinkage kinetics of the light‐curing adhesives or composites. Consequently, a reduced amount of marginal failure and microleakage in in vitro experiments were found 8…”

Section: Resultsmentioning

confidence: 99%

“…The mechanical properties were determined after immersing the specimens in water for 24 h at 37°C. The determination of linear polymerization shrinkage in dependence of irradiation time was performed with an apparatus of the University of Zurich, as described previously 8…”

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Polymerization of cyclic monomers. VII. Synthesis and radical polymerization of 1,3-bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes

Moszner

Zeuner

Völkel

et al. 1999

J. Appl. Polym. Sci.

Self Cite

View full text Add to dashboard Cite

1,3-Bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes 1 [RO: CH 3 O (a), C 2 H 5 O (b)] were synthesized by the esterification of the corresponding 1-alkoxycarbonyl-2-vinylcyclopropane-1-carboxylic acids with resorcinol. The structure of the new vinylcyclopropanes was confirmed by elemental analysis and infrared (IR), 1 H nuclear magnetic resonance ( 1 H-NMR), and 13 C nuclear magnetic resonance ( 13 C-NMR) spectroscopy. The radical polymerization of difunctional 2-vinyl-cyclopropanes in bulk with 2,2Ј-azoisobutyronitrile (AIBN) results in hard, transparent, crosslinked polymers. During the bulk polymerization of the crystalline bis[(1-methoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzene 1a, an expansion in volume of about 1% took place. The radical solution polymerization of 1a resulted in a soluble polymer with pendant 2-vinylcyclopropane groups.

show abstract

Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Polymerization of cyclic monomers. VII. Synthesis and radical polymerization of 1,3-bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes

Moszner

Zeuner

Völkel

et al. 1999

J. Appl. Polym. Sci.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Finally, one of the most promising approaches to reducing polymerization stress consists in the replacement of the commonly used methacrylates by cyclic monomers . Indeed, ring‐opening polymerization of monomers such as epoxy‐functionalized siloxanes, spiro orthocarbonates, cyclic acetals, oxetanes, or vinylcyclopropanes (VCPs) leads to a significant reduction in shrinkage compared to that of conventional methacrylates. Among these cyclic monomers, 1,1‐disubstituted 2‐VCPs were found to be particularly interesting .…”

Section: Introductionmentioning

confidence: 99%

Development of low‐shrinkage composites based on novel crosslinking vinylcyclopropanes

Tauscher

Catel

Fässler

et al. 2017

J of Applied Polymer Sci

Self Cite

View full text Add to dashboard Cite

Polymerization shrinkage of methacrylate-based dental composites remains a major concern in restorative dentistry. Cyclic monomers that undergo ring-opening polymerization are known to exhibit reduced polymerization shrinkage compared to methacrylates. In this article, the synthesis of four crosslinking 1,1-disubstituted 2-vinylcyclopropanes bearing rigid spacers is described. These monomers were synthesized by esterification of 1-ethoxycarbonyl-2-vinylcyclopropane-1-carboxylic acid with the corresponding diols. The photopolymerization kinetics of these monomers was investigated by photo-differential scanning calorimeter using bis(4-methoxybenzoyl)diethylgermane as the photoinitiator. The synthesized vinylcyclopropanes (VCPs) were shown to be more reactive than the frequently used reactive diluent triethylene glycol dimethacrylate. Composites based on these VCPs showed good mechanical properties and exhibited a significantly reduced volumetric shrinkage and shrinkage stress compared to a corresponding dimethacrylatebased restorative material. This work highlights the excellent potential of VCPs as alternatives to methacrylates in the development of low-shrinkage dental composites.

show abstract

Synthesis and Photopolymerization of Thiol‐Modified Triazine‐Based Monomers and Oligomers for the Use in Thiol‐Ene‐Based Dental Composites

Reinelt

Tabatabai

Moszner

et al. 2014

Macro Chemistry & Physics

Self Cite

View full text Add to dashboard Cite

Thiol‐ene photopolymerizations combine the unique features of step‐growth reactions and photoinitiated polymerizations, so that they experience a growing interest for applications such as coatings or dental restoratives. Most studies have making use of a relatively flexible ester and the hydrolytically labile derivative pentaerythritoltetra(3‐mercaptopropionate) (PETMP) as the thiol component in common. In this study, the performance of hydrolytically stable 1,3,5‐tris(3‐mercaptopropyl)‐1,3,5‐triazine‐2,4,6‐trione (4a), 1,3,5‐tris(2‐methyl‐3‐mercapto‐propyl)‐1,3,5‐triazine‐2,4,6‐trione (4b), and oligomers thereof in thiol‐ene photopolymerizations is investigated. The oligomers are prepared via thiol‐Michael or thiol‐isocyanate additions by using 4a and suitable diacrylates or diisocyanates containing a rigid core structure. Compared with PETMP, the thiol derivative 4a shows better flexural strength and modulus of elasticity in thiol‐ene photopolymerizations with 1,3,5‐triallyl‐1,3,5‐triazine‐2,4,6‐trione (TATATO) as the‐ene derivative. This phenomenon becomes especially evident after storage in water at 37 °C for 24 h. Furthermore, the performance regarding the flexural strength, the Young's modulus of elasticity, the polymerization shrinkage stress of 4a, and the polyadducts thereof in dental filling composites is evaluated and discussed.

show abstract

Synthesis and polymerization of vinylcyclopropanes

Cited by 31 publications

References 0 publications

Polymerization of cyclic monomers. VII. Synthesis and radical polymerization of 1,3-bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes

Polymerization of cyclic monomers. VII. Synthesis and radical polymerization of 1,3-bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes

Development of low‐shrinkage composites based on novel crosslinking vinylcyclopropanes

Synthesis and Photopolymerization of Thiol‐Modified Triazine‐Based Monomers and Oligomers for the Use in Thiol‐Ene‐Based Dental Composites

Contact Info

Product

Resources

About